136840-11-4

Basic information

• Product Name: Propanedioic acid, [1-(1-bromo-1-methylethyl)-3-hydroxy-3-phenyl-2-propenylidene]-, dimethyl ester
• CAS NO: 136840-11-4
• Molecular Formula: C17H19BrO5
• Molecular Weight: 383.239
• Mol File: 136840-11-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, [1-(1-bromo-1-methylethyl)-3-hydroxy-3-phenyl-2-propenylidene]-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, [1-(1-bromo-1-methylethyl)-3-hydroxy-3-phenyl-2-propenylidene]-, dimethyl ester(136840-11-4)
• EPA Substance Registry System: Propanedioic acid, [1-(1-bromo-1-methylethyl)-3-hydroxy-3-phenyl-2-propenylidene]-, dimethyl ester(136840-11-4)

Safety Data

• Hazardous Substances Data: 136840-11-4(Hazardous Substances Data)

Upstream product

• 87064-07-1 4-bromo-4-methyl-1-phenyl-pent-1-yn-3-one 
• 108-59-8 malonic acid dimethyl ester 

Relevant articles and documents

Functional Group Hybrids. Reactivity of α'-Nucleofuge α,β-Unsaturated Ketones. 2. Reactions with Malonate Anion. Concerning the Mechanism of the Favorskii Rearrangement

The scope and limitations of the reaction of α'-nucleofuge α,β-unsaturated ketones with sodium dimethyl malonate has been studied systematically.The substrates with good nucleofuges (halides, mesylate) give cyclopropanols upon reaction with malonate anion by way of a conjugate Favorskii reaction.In reactions with substrates containing the poorer nucleofuge (acetoxy) conjugate addition proceeded without entering the Favorskii manifold.Concerning the mechanism of the Favorskii reaction, it is suggested that the loss of the nucleofuge occurs to give a 2-oxyallyl cation, but that disrotatory ring closure is facile and the only products observed result from nucleophilic trapping of cyclopropanones to yield cyclopropanols in fair to good yield.